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What if hiring smart people and getting out of your way was not enough to build a self-managing agency? Today's featured guest will talk through the decisions most agency owners get wrong: when to stay involved, when to let go, and how the absence of rigor compounds into structural problems you won't even notice until you're stuck.

He'll talk about how bad hiring decisions led him to become the bottleneck, how he's trying to fix that, as well as why your "number" for how much your agency is worth is probably based on nothing, and the one financial habit that gives you genuine optionality.

Scott Leff is the founder of Leff, a B2B content marketing agency serving global professional services firms and nonprofits for over 16 years. His background spans business communications working as a managing director for a big brand, as well as a 22-month stint leading communications for Chicago's bid for the 2016 Olympic Games.

When the bid failed in the first round, he found himself in a period of reinvention. With the gig economy just taking off, he decided it was time to hang up his shingle. He started to take freelance work, which eventually led to hiring and forming his own business. This agency grew steadily, exploded during COVID, and is now navigating the reassessment most established agencies are facing in a shifting market.

In this episode, we'll discuss:

Why becoming the bottleneck isn't always about control
The hiring rigor every owner should have
Which metrics are you tracking? Why declining revenue doesn't equal failure

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Sponsors and Resources

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Knowing What You Should Never Have Delegated

For the first ten-plus years of his agency business, every meaningful decision flowed through Scott or his business partner. That wasn't always a problem, but as the agency grew and decision-making had to push down through a management layer, cracks formed. Not because the team was incapable, but because they were being handed authority without the context, direction, or support to use it well.

Hiring is the clearest example Scott points to. He gave department managers the autonomy to bring in their own people, which was a reasonable call on paper. But in a culture-driven organization like an agency, where your people are both your product and 80% of your overhead, that's the one decision you can't outsource and expect to get right. The fix wasn't micromanaging the process. It was figuring out the specific places where the founder's perspective is irreplaceable, and staying in the conversation there, even when it's uncomfortable to be involved.

Hiring Rigor Is Not Optional and Most Agencies Are Winging It

Scott attended a conference session led by someone who'd overseen hiring at Amazon and other large organizations. The biggest takeaway was a story about Jeff Bezos showing up to a debrief with three to four pages of handwritten notes on candidates, while everyone else showed up with nothing. That level of intentionality is what most agencies are missing entirely.

The real problem isn't that agency owners don't care about hiring. It's that they go in underprepared, unclear on exactly what they're looking for, leaning on gut instinct, and writing role descriptions that don't reflect the actual job.

To ensure you're getting applications from candidates that truly align with your agency and the required role, every part of the hiring process should be a test. Attention to detail? Bury the real application instructions at the bottom of the job post and see who finds them. Hiring a senior exec? Don't tell them much, give them a week and ask them to come back with a 90-day success plan. If they dive into answers before they ask a single question, that tells you everything. The point isn't the process for its own sake. It's that rigor on the front end reduces the cost of being wrong, and in an agency, being wrong on a hire is expensive for a long time.

Watch Who You're Hiring From: Big Agency Talent Doesn't Always Travel Well

There's a version of agency hiring that looks like a smart move: pull experienced people from larger, more established shops and let them install what's already working somewhere else. Here's why that doesn't work: You end up with talented people who are skilled at operating inside infrastructure, not building it. When there's no large team to direct, no resource pool to draw from, no SOP baked in for the last decade, they stall. The answer when things aren't cut and dried can be "that's not my job." And then it's nobody's job.

Scott saw a version of this play out during the Olympic bid. Big consulting firms had seconded teams into the organization, and the ones who thrived were the ones who could operate in ambiguity. The ones who couldn't were waiting for a structure that was never going to show up. The lesson isn't that experienced people from large agencies are bad hires. It's that the ability to figure things out without a system to lean on is the filter. And you have to test for it explicitly, because someone's resume will not tell you whether they have it.

Declining Revenue Doesn't Equal Failure, but You Have to Know What You're Actually Measuring

Your revenue may seem like the only metric that felt like it matters when it's going up every year. However, a modest drop of five or ten percent, can be a big psychological blow even though profit improves and client impact is strong. That's a vanity metric doing its job: making growth feel like identity.

Scott hit a similar inflection point when a former client asked him a simple question, why are you growing? Scott didn't have a clean answer. He'd been operating on the assumption that growth was inherently the goal, not a means to something else. The conversation points to a structural reality: if revenue is the only number you track, you'll optimize for it even when it costs you margin, leverage, and time. The healthier question is whether the agency is building toward the outcome you actually want, more optionality, a sellable asset, or just more control over your calendar. Revenue is a lagging indicator of that. Not the scoreboard.

The Decision to Sell Your Agency Has Nothing to Do With Your Number

Most agency owners carry a number in their head of what they want to walk away with when they sell. The problem is that the number is usually arbitrary, the market timing is unpredictable, and nobody warned the...